Chapter 2

Advanced Problems in Organic Chemistry for Competitive Examinations · 59 exercises

Problem 5

The total number of structural isomers of \(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\) would be (a) 4 (b) 8 (c) 5 (d) 10

6 step solution

Problem 7

How many geminal dichloride with different formula are possible for \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\) ? (a) only one (b) two (c) three (d) four

5 step solution

Problem 8

What is the relation between 3-ethylpentane and 3-methylhexane? (a) Chain isomers (b) Position isomers (c) Functional isomers (d) Metamers

5 step solution

Problem 10

The compounds \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) represent (a) chain isomerism (b) position isomerism (c) functional isomerism (d) all of the above

5 step solution

Problem 11

An isomer of ethanol is (a) methanol (b) acetone (c) diethyl ether (d) dimethyl ether

7 step solution

Problem 12

The number of primary, secondary and tertiary amines possible with the molecular formula \(\mathrm{C}_{3} \mathrm{H}_{9} \mathrm{~N}\) respectively (a) \(1,2,2\) (b) \(1,2,1\) (c) \(2,1,1\) (d) \(3,0,1\)

5 step solution

Problem 16

Identify specific rotation of a mixture have \(5 \mathrm{~g}\) of \((+) 2\) -butanol and \(7 \mathrm{~g}\) of \((-) 2\) -butanol (If specific rotation of \(100 \%\) pure compound is \(13.5^{\circ}\) ) (a) \(-2.25^{\circ}\) (b) \(-1.6^{\circ}\) (c) \(12.2^{\circ}\) (d) \(4.45^{\circ}\)

6 step solution

Problem 17

Which compound is not the isomer of 3 -ethyl-2-methylpentane?

3 step solution

Problem 24

Identify compounds that give geometrical isomerisation

4 step solution

Problem 25

Which conformation has a \(\mathrm{C}_{3}\) axis of symmetry? (a) Boat (b) Twist boat (c) Chair (d) Enveloped

3 step solution

Problem 26

Which of the following can show tautomerism? (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CNO}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (c) \(\mathrm{R}_{3} \mathrm{CNO}_{2}\) (d) \(\mathrm{RCH}_{2} \mathrm{NO}_{2}\)

4 step solution

Problem 28

Choose the total number of constitutional isomers with the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\). (a) 9 (b) 7 (c) 5 (d) 3

7 step solution

Problem 28

Which will not show tautomerism? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NO}_{2}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{NO}_{2}\) (c) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{NO}_{2}\)

5 step solution

Problem 29

Which of the following compound show tautomerism? (a) \(\left(\mathrm{H}_{3} \mathrm{C}\right)_{2} \mathrm{CCl}-\mathrm{CH}=\mathrm{CH}_{2}\) (b) O=Cc1ccccc1 (c) \(\left(\mathrm{H}_{3} \mathrm{C}\right)_{2} \mathrm{C}\left(\mathrm{NO}_{2}\right)-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO}\) (d) None of these

3 step solution

Problem 30

In which structure Gauche form has less potential energy than antiform (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}+\mathrm{CH}_{2}-\mathrm{Cl}\) (b) \(\mathrm{HO}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{F}\) (c) \(\mathrm{CH}_{2}\) ) \(\mathrm{CH}_{2}\) (d) \(\mathrm{HO}-\mathrm{CH}_{2}+\mathrm{CH}_{2}-\mathrm{OH}\)

4 step solution

Problem 31

Tautomerism will be exhibited by (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CNO}\) (c) \(\mathrm{R}_{3} \mathrm{CNO}_{2}\) (d) \(\mathrm{RCH}_{2} \mathrm{NO}_{2}\)

6 step solution

Problem 32

Which of the following is not an example of tautomeric equilibrium? (a) \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{C}=\mathrm{O} \rightleftharpoons \mathrm{CH}_{2}-\mathrm{CH}=\mathrm{C}-\mathrm{O}\) (b) \(-\mathrm{N}=\mathrm{N}-\mathrm{NH} \rightleftharpoons \mathrm{NH}-\mathrm{N}=\mathrm{N}\) (c) \(>\mathrm{CH}-\mathrm{N}=\mathrm{O} \rightleftharpoons>\mathrm{C}=\mathrm{N}-\mathrm{OH}\) (d) \(-\mathrm{NH}-\mathrm{C}=\mathrm{O} \rightleftharpoons-\mathrm{N}=\mathrm{C}-\mathrm{OH}\)

6 step solution

Problem 37

Geometrical isomers differ in (a) position of functional group (b) spatial arrangement of atoms (c) position of atoms (d) length of carbon chain

3 step solution

Problem 38

Stereoisomers have different (a) Molecular formula (b) Structural formula (c) Configuration (d) Molecular mass

5 step solution

Problem 41

Which compound can show geometrical isomerism? (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\)

5 step solution

Problem 50

The number of geometrical isomers in the following compound is \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{C}_{2} \mathrm{H}_{5}\) (a) 4 (b) 3 (c) 2 (d) 5

4 step solution

Problem 52

Identify compound(s) in which gauche conformer is more stable than staggered (a) 1,2 -difluoroethane (b) Chloropropane (c) Ethylene glycol (d) Succinic acid

5 step solution

Problem 52

What characteristic is the best common to both cis-2-butene and trans-2-butene? (a) B.P. (b) Dipole moment (c) Heat of hydrogenation (d) Product of hydrogenation

5 step solution

Problem 58

The number of optically active compounds in the isomers of \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Br}\) is (a) 1 (b) 2 (c) 3 (d) 4

4 step solution

Problem 60

The number of optically active isomers observed in 2,3 -dichlorobutane is (a) 0 (b) 2 (c) 3 (d) 4

5 step solution

Problem 64

The instrument which can be used to measure optical activity, i.e., specific rotation (a) Refractometer (b) Photometer (c) Voltmeter (d) Polarimeter

3 step solution

Problem 72

Identify the structure of Erythro-butane-2, 3-diol

5 step solution

Problem 73

The enantiomeric excess and observed specific rotation of a mixture containing \(6 \mathrm{~g}\) of \((+)-2\) -butanol and \(4(\mathrm{~g})\) of \((-)-2\) -butanol are respectively (If the specific rotation of enantiomerically pure \((+)-2\) -butanol is \(+13.5\) units) (a) \(80 \%\), \(+2.7\) unit (b) \(20 \%,-27\) unit (c) \(20 \%,+2.7\) unit (d) \(80 \%\), \(-27\) unit

5 step solution

Problem 74

Which of the following pair of isomers cannot be separated by fractional crystallisation or fractional distillation? (a) Maleic acid and fumaric acid (b) (+)-Tartaric acid and meso-tartaric acid (c) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{COOH}\) and \(\mathrm{H}_{2} \mathrm{~N}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{COOH}\) CC(N)C(=O)O (d) ( \(+\) )-lactic acid and (-)-lactic acid

7 step solution

Problem 75

Increasing order of stability among the three main conformation (i.e., eclipse, anti, gauche) of ethylene glycol is (a) Eclipse, gauche, anti (b) Gauche, eclipse, anti (c) Eclipse, anti, gauche (d) Anti, gauche, eclipse

5 step solution

Problem 79

In the Newman projection formula of the least stable staggered form of \(\mathrm{n}\) -butane, which of the following reasons is the causes of its unstability? (a) Van der Waal's strain (b) Torsional strain (c) Combination of both (d) None of these

4 step solution

Problem 81

The dihedral angle between two methyl groups in partially eclipsed conformation of n-butane is (a) \(180^{\circ}\) (b) \(120^{\circ}\) (c) \(90^{\circ}\) (d) \(109^{\circ} 28^{\prime}\)

3 step solution

Problem 84

Evaporation of an aqueous solution of ammonium cyanate gives urea. This reaction follows the class of (a) Polymerisation (b) Isomerisation (c) Association (d) Dissociation

4 step solution

Problem 85

The possible number of alkynes with the formula \(\mathrm{C}_{5} \mathrm{H}_{8}\) is (a) 2 (b) 3 (c) 4 (d) 5

4 step solution

Problem 86

How many isomers of \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{OH}\) will be primary alcohols (a) 2 (b) 3 (c) 4 (d) 5

4 step solution

Problem 87

Identify the compounds that give trans product on reaction with alcoholic KOH and heat

6 step solution

Problem 87

Number of isomeric forms of \(\mathrm{C}_{7} \mathrm{H}_{9} \mathrm{~N}\) having benzene ring will be (a) 7 (b) 6 (c) 5 (d) 4

5 step solution

Problem 88

Which of the following is an isomer of diethyl ether (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\mathrm{CH}_{3} \mathrm{CHO}\) (c) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\) (d) \(\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{CHOH}\)

4 step solution

Problem 89

Total number of isomeric alcohols with the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) is (a) 1 (b) 2 (c) 3 (d) 4

5 step solution

Problem 90

Different spatial arrangements of the atom that result from restricted rotation about a single bond are conformers. The general stability order of these conformer are as follows. Anti \(>\) Gauch \(>\) Partially eclipsed \(>\) Fully eclipsed Although anti is more stable than gauch but in some cases gauch is more stable than anti. Number of possible stable conformers of butane is (a) 2 (b) 4 (c) 6 (d) Infinite

4 step solution

Problem 90

The molecular formula of a saturated compound is \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}\). The formula permits the existence of two (a) functional isomers (b) position isomers (c) optical isomers (d) cis-trans isomers

5 step solution

Problem 91

The type of isomerism found in urea molecule is (a) Chain (b) Position (c) Tautomerism (d) None of these

4 step solution

Problem 92

An alkane can show structural isomerism if it has ......... number of minimum carbon atoms (a) 1 (b) 2 (c) 3 (d) 4

5 step solution

Problem 93

How many chain isomers can be obtained from the alkane \(\mathrm{C}_{6} \mathrm{H}_{14} ?\) (a) 4 (b) 5 (c) 6 (d) 7

5 step solution

Problem 97

In the reaction: \(\mathrm{CH}_{3} \mathrm{CHO}+\mathrm{HCN} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CN}\) a chiral centre is produced. The number of stereoisomers of the product is (a) 3 (b) 2 (c) 4 (d) none of these

4 step solution

Problem 98

Among the following conformers, which has highest potential energy for \(\mathrm{n}\) -butane (along \(\mathrm{C}_{2}-\mathrm{C}_{3}\) bond rotation)? (a) Skew (b) Fully eclipsed (c) Staggered (d) Partially eclipsed

4 step solution

Problem 98

The molecule 3 -penten-2-ol can exhibit (a) Optical isomerism (b) Geometrical isomerism (c) Metamerism (d) Tautomerism The correct answer is (a) (a) and (b) (b) (a) and (c) (c) (b) and (c) (d) (a) and (d)

6 step solution

Problem 99

Find the total number of isomers (including stereo isomers) in dimethyl cyclopropane and dimethyl cyclobutane (a) 6,8 (b) 5,6 (c) 4,5 (d) 4,6

3 step solution

Problem 104

Racemic mixture is formed by mixing two (a) Isomeric compounds (b) Chiral compounds (c) Meso compounds (d) Enantiomers

3 step solution

Problem 105

Which of the following does not show geometrical isomerism? (a) 1,2 -dichloro-1-pentene (b) 1,3 -dichloro-2-pentene (c) 1,1-dichloro-1-pentene (d) 1,4 -dichloro-2-pentene

6 step solution

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